5-Hydroxyindoleacetic Acid → 2-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide

참여 물질

역할	이름	HCID	투입량
반응물	5-Hydroxyindoleacetic Acid	HCID 1826	—
반응물	Diisopropylethylamine	HCID 81531	—
반응물	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
반응물	2-phenyl-1-(1-phenyl-1H-1,2,3-triazol-5-yl)ethanamine	HCID 90281247	—
용매	Dimethylformamide	HCID 6228	—
생성물	2-(5-hydroxy-1H-indol-3-yl)-N-[2-phenyl-1-(3-phenyltriazol-4-yl)ethyl]acetamide	HCID 90281276	—

반응 단계

HATU (40 mg, 0.105 mmol) was added to a solution of 2-(5-hydroxy-1H-indol-3-yl)acetic acid (19.2 mg, 0.1 mmol) and DIPEA (0.02 mL, 0.12 mmol) in DMF (0.3 mL). After 10 minutes, 9D (26.5 mg, 0.1 mmol) in 0.2 mL of DMF was added to the reaction. The reaction was stirred for 2 hours. LC/MS shows desired product with a small amount of acid. Purified reaction mixture on prep reverse phase HPLC using 20-80% B over 20 min. (A=0.1% TFA/H2O; B=0.1% TFA/Acetonitrile). Combined pure fractions as determined by LC/MS and lyophilized to provide the desired product. 1H NMR (400 MHz, CD3OD) δ 7.76 (s, 1H), 7.47 (t, J=7.5 Hz, 1H), 7.39 (t, J=7.6 Hz, 2H), 7.21-7.01 (m, 6H), 6.96 (s, 1H), 6.84 (d, J=1.9 Hz, 1H), 6.78 (d, J=6.8 Hz, 2H), 6.68 (dd, J=8.6, 2.3 Hz, 1H), 5.46 (s, 2H), 5.21 (t, J=7.6 Hz, 1H), 2.96 (ddd, J=21.5, 13.3, 7.6 Hz, 2H); MS (m/z) 438 [M+H]+.

출처 및 근거

DOI	10.6084/m9.figshare.5104873.v1
특허 번호	US09220710B2
출처 데이터셋	uspto-grants-2015_12
ORD ID	ord-b9a3c52a6e754d8fb0397816574848a6
출처 메모	uspto-grants-2015_12